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411744

Sigma-Aldrich

1,4-Butanediol diacrylate

technical grade, contains ~75 ppm hydroquinone as inhibitor

Synonym(s):

1,4-Bis(acryloyloxy)butane, Tetramethylene diacrylate

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About This Item

Linear Formula:
(H2C=CHCO2CH2CH2-)2
CAS Number:
Molecular Weight:
198.22
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

grade

technical grade

Quality Level

Assay

87%

form

liquid

contains

~75 ppm hydroquinone as inhibitor

refractive index

n20/D 1.456 (lit.)

bp

83 °C/0.3 mmHg (lit.)

density

1.051 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=CC(=O)OCCCCOC(=O)C=C

InChI

1S/C10H14O4/c1-3-9(11)13-7-5-6-8-14-10(12)4-2/h3-4H,1-2,5-8H2

InChI key

JHWGFJBTMHEZME-UHFFFAOYSA-N

General description

1,4-Butanediol diacrylate(BDDA) is an acrylate monomer and a multifunctional crosslinking agent. It ​has a relatively low viscosity and undergoes photopolymerization, initiated by UV radiation. BDDA contributes to the flexibility and elasticity of the cured materials. It is used in optical films,3D printing, tissue engineering, dental composites, UV-curable adhesives, and sealants.

Application

1,4-Butanediol diacrylate can be used:



  • As a precursor to synthesize joint-linker hydrogels with good mechanical strength and used as scaffold materials in bone tissue engineering as biomimetics for natural tissues and also in drug delivery systems.
  • To prepare anti-fouling coating for dental composites.
  • As a crosslinking agent to prepare hydrophobic acrylic intraocular lens(IOL) materials with reduced glistening.
  • As a precursor to fabricate poly(β-amino ester) based solid polymer electrolytefilms for Li-ion batteries. BDDA enhances the ionic conductivity of theelectrolyte films.

Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1A

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

>235.4 °F

Flash Point(C)

> 113 °C


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Y Sakai et al.
Bioscience, biotechnology, and biochemistry, 63(4), 688-697 (1999-06-11)
A carboxylesterase that is responsible for conversion of 1,4-butanediol diacrylate (BDA) to 4-hydroxybutyl acrylate (4HBA) was found in Brevibacterium lines IFO 12171, and purified to homogeneity. The purified enzyme was active toward a variety of diesters of ethylene glycol, 1,4-butanediol
Swelling studies of super water retainer acrylamide/crotonic acid hydrogels crosslinked by trimethylolpropane triacrylate and 1, 4-butanediol dimethacrylate.
Karadag E and Saraydin D
Polymer Bull., 48(3), 299-307 (2002)
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Acta biochimica et biophysica Sinica, 38(11), 780-787 (2006-11-09)
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